Reacción #3425

Ecuación de reacción

3-Iodo-4-methylpyridine

t-BuLi

1,2,3,5,6,7-hexahydropyrrolizinium perchlorate

→

title compound

Rendimiento 6.5%

7a-(4-methyl-3-pyridinyl)-hexahydro-1H-pyrrolizine

Rendimiento 6.5%

Disolventes

Et2O

pentane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to -10° C.
2. 2
   OtroThe cold bath was removed
3. 3
   workup.ADDITION2N HCl was added
4. 4
   Otrothe phases were separated
5. 5
   Extracciónextracted with CH2Cl2 (2×)
6. 6
   Secadodried (MgSO4)
7. 7
   Concentraciónconcentrated
8. 8
   Otrothe residue was chromatographed (silica gel; CHCl3 /MeOH, 99:1)

Procedimiento

3-Iodo-4-methylpyridine (330 mg, 3.10 mmol) was dissolved in Et2O and cooled to -95° C. A solution of t-BuLi (1.7M in pentane, 4.0 ml, 6.80 mmol) in pentane was added dropwise. 1,2,3,5,6,7-hexahydropyrrolizinium perchlorate (960 mg, 4.60 mmol) was added, and the reaction mixture was allowed to warm to -10° C. with stirring for 2 hours. The cold bath was removed, 2N HCl was added, and the phases were separated. The aqueous phase was basified with 15% NaOH and extracted with CH2Cl2 (2×). The CH2Cl2 fractions were combined, dried (MgSO4) and concentrated, and the residue was chromatographed (silica gel; CHCl3 /MeOH, 99:1) to afford the title compound as an oil (41 mg, 6%): 1H NMR (CDCl3, 300 MHz) δ1.54-1.69 (m, 2H), 1.77-1.89 (m, 2H), 1.93-2.11 (m, 4H), 2.41 (s, 3H), 2.69-2.77 (m, 2H), 3.08-3.15 (m, 2H), 7.02 (d, J=4.8 Hz, 1H), 8.32 (d, J=4.8 Hz, 1H), 9.06 (s, 1H); MS (CI/NH3) m/z: 203 (M+H)+.

Fuente